Total Synthesis of Naturally Occurring 5,7,8-Trioxygenated Homoisoflavonoids

Sangil Kwon, Sanha Lee, Myunghoe Heo, Bit Lee, Xiang Fei, Timothy W. Corson, Seung Yong Seo

Research output: Contribution to journalArticle

Abstract

Homoisoflavonoids are in the subclass of the larger family of flavonoids but have one more alkyl carbon than flavonoids. Among them, 5,7,8-trioxygenated homoisoflavonoids have not been extensively studied for synthesis and biological evaluation. Our current objective is to synthesize 2 5,7,8-trioxygenated chroman-4-ones and 12 5,7,8-trioxygenated homoisoflavonoids that have been isolated from the plants Bellevalia eigii, Drimiopsis maculata, Ledebouria graminifolia, Eucomis autumnalis, Eucomis punctata, Eucomis pallidiflora, Chionodoxa luciliae, Muscari comosum, and Dracaena cochinchinensis. For this purpose, 1,3,4,5-tetramethoxybenzene and 4′-benzyloxy-2′,3′-dimethoxy-6′-hydroxyacetophenone were used as starting materials. Asymmetric transfer hydrogenation using Noyori's Ru catalyst provided 5,7,8-trioxygenated-3-benzylchroman-4-ones with R-configuration in high yield and enantiomeric excess. By selective deprotection of homoisoflavonoids using BCl3, the total synthesis of natural products including 10 first syntheses and three asymmetric syntheses has been completed, and three isomers of the reported dracaeconolide B could be provided. Our research on 5,7,8-trioxygenated homoisoflavonoids would be useful for the synthesis of related natural products and pharmacological applications.

Original languageEnglish (US)
Pages (from-to)11043-11057
Number of pages15
JournalACS Omega
Volume5
Issue number19
DOIs
StatePublished - May 19 2020

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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